The Final Days of Obama’s Tech Surge

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On November 9, 2016, some members of the United States Digital Service — President Obama’s shining example of how Silicon Valley’s tech minds can make a palpable impact on government — got up early to attend a retreat at Camp David. It was supposed to be a celebration of all the team had done in its two-year history—a reward for amazing work, and a planning session for the remainder of the term and the transition to the next. From its origins as a small tiger team parachuting into a terrible government IT crisis — the HealthCare.gov debacle — the USDS had grown to 202 members spread between its headquarters and six agencies. In fact, the organization couldn’t fit into the relatively intimate presidential dacha, and the retreat was to be split into two sessions a week apart. But because this first event came the day after the election of Donald J. Trump as the next president, the event was less a celebration than a wake. Many participants were openly weeping. Their leaders desperately tried to compose themselves, and gave encouraging speeches that might somehow maintain morale. But despite the bravado, they themselves harbored terrible fears about the future of the USDS, if not the country they had been tirelessly serving for the past few months and years.

Barack Obama was a president who understood not only how technology could transform the way government services worked, but also technology itself. He got it. He could assess an elevator pitch at a small-business fair with the acumen of a Sand Hill Road VC. He could gab with MIT Media Lab leader Joi Ito about artificial intelligence. He even hosted a mini South by Southwest on the White House lawn. And he regarded his tech teams as a pet project, providing them the ultimate air cover when they got caught up in the merciless wheels of government bureaucracy or just plain obstinacy.

He will now be succeeded by a president whose knowledge of what he calls “the cyber” seems limited to late-night tweeting and a vision of hackers as overweight adolescents invading the DNC from their bedrooms. Hillary Clinton had announced in her official policy statement that if elected she would be an enthusiastic supporter of the USDS and other aspects of what came to be known as the Obama Tech Surge. Its members thought of themselves as completing the first laps of an epic relay race. Now no one knows whether there will be a baton handoff at all.

The team fears not only for its legacy but also for its fellow citizens. Better than anyone, its members have come to understand how important their work is. They have enabled veterans to process disability claims, aided immigrants in obtaining green cards, helped citizens securely access their tax information, and run a bug bounty program for the Pentagon. If you have gotten insurance from HealthCare.gov, figured out which university to attend through the Department of Education’s College Scorecard, or had your military health records moved to the Veteran’s Administration without a hitch, the USDS has made a difference in your life. Its continued existence means that in the future, the way you access government services — the stuff you pay for with your taxes — will operate more like Jeff Bezos than Franz Kafka.

Though the effort is presumably bipartisan — who would object to using technology to improve government and save money? — there is no guarantee that Donald Trump will continue it.

In the weeks after the election, I began a series of interviews with the Obama tech team, including the USDS, its sister tech rehab group in the General Services Administration called 18F, CTO Megan Smith and her deputies, and Obama’s digital communications team led by former Twitter executive Jason Goldman. I also spoke to a number of former team members. Publicly, almost all of them expressed optimism that the work would continue: The transition was proceeding cordially, the efforts to reform government IT were bipartisan, and Congress would back their efforts, which had already saved money for taxpayers and delivered services for citizens. But lurking behind every statement was an existential dread that Donald Trump would either pull the plug on one of the great achievements of the last eight years, or worse — he might order the best and brightest to work on projects that violated their moral codes.

If those fears were confirmed, it would mean the end of one of the most inspiring developments in government in years — and a backwards step for a bureaucracy that had for too long ignored the nation’s most powerful tools.

Barack Obama came to the White House in 2009 with soaring expectations in the tech realm. He was close to the iconic digital firms, and shared their mindset that chips and algorithms, mixed with a can-do spirit, can work magic. It was widely assumed that for the first time, the Silicon Valley ethos and knowhow would truly be woven into a government that seemed to be operating on your grandfather’s tech platforms. “He campaigned on it,” says Thomas Kalil, a science and tech policy specialist from the Clinton era who joined the Obama administration. “He understood the critical role it could play in virtually every goal he wanted to achieve.” Obama tinkered with the White House Office of Science and Technology Policy (OSTP), creating new roles and duties. For the first time, the nation would have a chief technology officer and a chief information officer (based within the Office of Management and Budget). For good measure, he included a chief data officer.

But tech policy geeks were disappointed by Obama’s first term. “We came in hoping to make big changes in broadband, the smart grid, and health information systems,” says Andrew McLaughlin, a former Google policy head who was a deputy CTO. He acknowledges that the high expectations weren’t met. “It was hard to argue that [tech policy] was a reasonable priority when you’ve got two wars and a national economic catastrophe,” he says.

Then, in March 2012, a dynamo named Todd Park become Obama’s second CTO. A health care entrepreneur and trained engineer, Park came from a successful stint as the CTO of Health and Human Services. One of the first things he helped create was a program called Presidential Innovation Fellows (PIF), bringing bright technologists into the White House. His choices would later play key roles in the coming Tech Surge.

In late 2012, Jennifer Pahlka, a friend of Park’s who heads Code for America, had visited the UK and returned ablaze with reports of how an insurgent digital team was reforming government there. Park convinced Pahlka to take a one-year post as deputy CTO, beginning in June 2013. She spent much of her time fighting to start what is now the United States Digital Service. Meanwhile, with the help of some PIFs, GSA was setting up its own group that would recruit smart coders and designers from private industry as sort of a service bureau for agencies requesting help on products. It was named 18F, after the GSA’s address. Though Pahlka thought that 18F was great, she envisioned a more ambitious effort, closer to the White House, with more authority.

Megan Smith

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Todd Park

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Then came October 2013, when technology — once supposed to be an Obama strength — almost took down his administration. The signature legislation of his presidency, the Affordable Care Act, depended on a website that matched individuals to health insurers. It was a thermonuclear failure. When Park swooped into the situation with some of his PIF team, he realized that the only solution was to tap outside talent. Drawing on connections to the Obama campaign’s digital warriors and Silicon Valley companies, Park tapped a very small group of great coders and developers to rebuild in weeks, on the fly, what $500 million worth of contractors and government employees couldn’t do.

In fact, an expensive, mishandled disaster was almost routine for government IT, where overpaid contractors with little oversight used outdated processes to work with jaded government workers. But this time the lifers had to cooperate. “The message that they got loud and clear from the White House was, This is bad enough that none of you is getting out of this alive,” Mikey Dickerson, a former Google engineer who led the team, later recalls. “Your only way out is if you get your act together and make the site work.”

Amazingly, they pulled off the rescue; ultimately, the website exceeded the estimated signups. HealthCare.gov did not become Obama’s Katrina, but rather his pivot into a full and lusty embrace of tech culture. Park seized the initiative and began recruiting to build up what is now the USDS. “There were several failed attempts, but we have HealthCare.gov to credit — it was a huge wakeup moment for everybody inside government from the president on down,” says Haley Van Dyck, who became deputy administrator. Her boss would be Dickerson, a droll, stocky pessimist who had become hooked on serving his country.

Over the next two and a half years, the USDS, along with 18F, would chalk up a series of victories, using small teams to take on vital projects. Meanwhile, a new kind of American hero emerged: a super-skilled techie who abandoned a trendy locale and a knapsack full of material rewards to work for low pay and under government restrictions — all for the idealistic mission of allowing people to access government services as smoothly as they use Amazon and Uber.

Matthew Weaver, a star Google engineer who worked on the original HealthCare.gov project and became an early USDS leader, says that the work transformed him. Every night he would check the dashboard to see how many people came to the page, opened an account, logged in, and then — the gold standard — actually signed up for insurance. “I could see this number, how many got health care,” he says. “Each number was a family. All the rest of my accomplishments evaporated. Working on the biggest machine of all time did not compare to getting people in the doctor’s office.”

In a technical sense, the work was straightforward. What made it difficult was bucking years of entrenched bureaucracy and a need to keep some current, outdated systems going because as bad as they were, real people depended on them. Some of the tasks had high-profile rewards, like resolving the stubborn divide between health records of the military and VA, combining dozens of VA sites into a single, well-organized home, or replacing the infuriating Pentagon travel system with something that actually worked. But even the more mundane projects made a difference. “If you can make things just a little easier, then you are rebuilding the trust between a government and its citizens,” says Kim Rachmeler, a former Amazon engineer who came out of retirement to become the USDS director of engineering, leading a team inside the Internal Revenue Service. Her squad fixed a huge security problem that exposed taxpayers to thieves every time they accessed tax history.

The presence of the Tech Surgers has actually stopped potential IT train wrecks before they happen. Take the example of a congressional mandate for HHS to drastically change the way it paid doctors for Medicare. This would affect about 600,000 clinicians treating 55 million people. It was a project parceled out to multiple contractors, and if a four-person USDS team hadn’t intervened it would have been as bad as the original HealthCare.gov disaster. “We looked at what they were doing and said, ‘This is unlikely to produce the thing you are hoping to produce,’” says Mina Hsiang, head of the USDS’s Digital Service at HHS. “Nobody ever looked at the demos of the products they were hiring people to build, so we showed them, and they said, ‘That’s awful!’”

The agency agreed to let a seven-person USDS team change or cancel many of the contracts, as well as simplify the project, which included a 900-page document outlining different ways physicians might be paid. They broke up the remaining process into pieces and launched pilot versions every two weeks, each time integrating a new rule (instead of the usual practice of shipping with everything in the program at once, which invariably would fail). Last October, the last version shipped, to great feedback both from inside government and out. And it came in $20 million under the original amount budgeted.

While some legislators celebrated the USDS and 18F, others questioned it, especially those close to the special interests who had formerly feasted on the bounty of fat contracts with little accountability. Some representatives testily asked why these organizations weren’t taking on the big projects — multi-billion dollar stuff like the massive FBI crime database or the humongous Social Security IT projects.

Those criticisms missed the point. The long-term goal of these teams was not to become the government’s tech employment service but rather to reform it. Though the USDS and 18F are assigned specific projects, the larger goal is to prove the efficacy of a contemporary information technology process called agile development. Agile is characterized by short sprints of coding, continual testing, and gradual rollouts. It’s a mindset deeply baked into the behavior of the giant tech companies that started in dorm rooms or garages and have scaled to tens of thousands. An agile process is built on collaboration, where the system progresses holistically. But Byzantine government practices had ignored it, ossifying into systems where different contractors each develop a piece of the puzzle, inevitably discovering late in the process that the pieces don’t fit. The tech surge also introduced other innovations long embraced by corporations, like cloud computing on private platforms owned by Amazon or Microsoft.

Todd Park recounts a conversation he had with a civil servant who had worked in Immigration Services for three decades. The USDS team inside the service had led a project to modernize the immigration form, moving it from paper documents to digital. The employee was gushing to Park about the sprints and user design approaches associated with the agile process. “She said to me, working with USDS and 18F teams to modernize immigration was the, quote, most transformative experience in her life, and she’s never going back to the old ways,” says Park, breaking into his high-pitched laugh.

Another possible benefit of modernization: protecting information. With devastating breaches like the Office of Personnel Management leak, Obama’s tenure will not be looked upon as a golden age of security. CIO Tony Scott says that updating the software base will make systems not only more efficient but also harder to crack. (While we’re in critique mode, I might also mention that one tech failing of this president has been his inability to put the cryptography controversy to rest.)

Last May a number of tech surge operations were combined in a GSA division called the Technology Transformation Service (TTS). It includes 18F, the Presidential Innovation Fellows program, a tech procurement program, a seed investment project, and a number of other services such as cloud computing. The TTS’s current commissioner (recruited by Todd Park, of course) is Rob Cook, a newcomer to government but not technology: He had previous been the VP of software development at Pixar, where he won an Oscar.

The office of the CTO has reflected the interests of a president who thinks a lot of about technology. Former Google executive Megan Smith, who succeeded Park as CTO in September 2014 (Park remained in government as a special assistant to the President), says she focused her tenure on three “buckets.” The first was injecting tech thinking into policy. Though the digital mindset is now recognized as essential in the private sector, government regards engineers only as people who implement plans, not as shapers of solutions. Her idea was to “put tech folks in the room,” an effort that she says is now in effect inside the White House and is spreading throughout government. The other two buckets deal in “capacity building” — bringing actual people and practices into government and the nation at large. The latter initiative deals with Smith’s deepest passion: encouraging diversity in STEM fields (science, technology, engineering, math). She’s created a program called TechHire, run hackathons and meetups, and made endless appearances on the subject; to augment those efforts, she brought in Laura Weidman Powers, head of Code 2040, a program inspiring Blacks and Latinxs to start tech careers.

“It feels like 1997 internet,” Smith says of the integration of tech thinking in government. “It’s going to be a big thing. Some people still say it’s like CB radios, but it is the beginning of digital, open-data-driven government, and it’s going to be sucked into everything. People are learning computational thinking. It hasn’t become the new normal, but it is definitely becoming it.”

Her deputies have helped establish that new normal. Chief Data Scientist DJ Patil explains that though government has always been a leader in data, from the intelligence agencies to weather, having a data science effort in the White House focuses government from the top. (Having a president who loves this stuff is a bonus.) “Data is in every single one of those [top-level] conversations. It’s no longer a back office thing, but it’s a front office policy component,” says Patil. He has used the presidential backing to pursue a program constructing a massive database to help assess how community policing works. Another deputy CTO, Princeton computer science professor Edward Felten, pulled together resources (building on early work by deputy CTO Alexander Macgillivray), for a massive government study of AI, a particular interest of this president. The work helped set policy for the US stance on developing, adjusting to, and maybe containing AI, at least so it wouldn’t kill us all.

No matter what Donald Trump decides to do with Obama’s tech effort, it is inconceivable that he will personally inspire its workers as this president has. Patil says that in meetings, Obama said things about technical subjects like software procurement, electronic medical records, or AI that exceeded the knowledge of experts in the room. “He reads extensively and knows the subjects,” he says. “He’s a deep believer in data.”

It’s pretty hard to picture Donald Trump engaging in geek talk on artificial intelligence, data science, and coding initiatives. But everyone in Obama’s tech surge thinks it that if logic prevails, the new leader—or at least his advisors—will maintain the momentum of the tech surge. “It’s like having a Tesla in the driveway,” says Macgillivray, referring to the USDS and the Tech Transformation Service. “It’s inconceivable to me that anyone wouldn’t use it.”

Mikey Dickerson and Haley Van Dyck.

Stephen Voss

In the last weeks of the Obama presidency, those in the USDS were working harder than ever. I met with its leaders at its headquarters in a row of federally owned three-story brownstones on Jackson Place, a frisbee toss away from the White House. The house was once home to Teddy Roosevelt’s family when the West Wing was under construction. In what might have been the Roosevelt dining room, there are rows of tables with engineers and product designers banging away on computers. In the basement is a conference room that is the only access to another workspace, and meetings are constantly interrupted by people passing through.

I’m meeting with Mikey Dickerson and Haley Van Dyck, both of whom, as presidential appointees, are on their way out. We are joined by Matt Cutts, who took a leave from his job as one of Google’s top search engineers (and who for years informally became the search team’s key communicator to the tech community) to join the USDS team in the Pentagon. Now Cutts has been appointed the USDS’s new director of engineering, which puts him in line to be the interim head of the service when Dickerson and Van Dyck leave. He’ll stay there until the Trump administration picks a new director — or shuts down the whole saloon. The expectation is that it will take a while for the incoming administration to even take stock of the effort, so there may be months of reprieves, during which the teams hope to be able to perform enough good work to convince the newcomers that the organization is indeed worth keeping, even if was cooked up in the Obama era.

A huge priority after the election for the USDS was documenting its accomplishments. In essence, it was preparing a brief to save its life. The focus of the effort was a report to Congress. In part a response to complaints from GOP legislators who were demanding “accountability” from the new service, the project took on added urgency after November, when it became clear that the new president would not be the candidate whose detailed tech policy gave shout-outs to Obama’s tech surge.

The 77-page (!) document dropped last Thursday, barely a week before most of its authors had to vacate the grounds. It joined a small body of here’s-why-you-shouldn’t-kill-us literature emanating from other Tech Surge outposts—the OSTP, 18F, et cetera— but this turned out to be a labor of love. Its 11 chapters each break down a major project, describing the necessity for each, the approach taken, the product delivered (complete with screen shots), and the lessons learned that might make future efforts easier and cheaper. Considering that a typical government IT project has traditionally involved hundreds of millions of dollars for a convoluted system that often never works at all, USDS’s bang for the bucks is impressive: its budget is only $14 million, with about an equal amount spent by the agencies in which some of its teams are embedded.

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The report plays down the meta aspiration of the Obama tech surge — to dig itself into the mind of government so deeply that it becomes a permanent change. Dickerson wants to see the USDS grow into not a huge bureaucracy but rather a nimble organization of small teams that parachute into agencies and make big things happen. His role model is the military Special Forces. “We’ve actually done a lot of studying with the JSOC folks, the Joint Special Operations Command,” he says. “They’re about 1,000 times bigger than we are, but they have a very similar problem — an organization that needs to respond to very quickly changing conditions, to be lean and share information very quickly.”

That won’t happen if the Trump team decides that the USDS, or even the whole tech surge, isn’t worth keeping. As the countdown clock to the next inauguration gets into the single digits, there’s still no clarity about what the newcomers are thinking. There have been both formal meetings with the Trump transition team and more informal meetings off-hours, held sub rosa off the grounds. At these, the Trump people — including some from the sphere of Peter Thiel, a key tech advisor — seemed familiar with the questions lobbed at the USDS and 18F, and posed them once again to the Obama people, who in turn pressed their case that they were making government work better. They made favorable noises at the justifications for the USDS activities. “I’ve been happy to hear that agenda taken seriously so far, but I am not taking it for granted,” says one insider involved in the talks. “We haven’t seen any action yet.” (One tipoff to the direction of the next regime — will the new CTO be an engineer?)

Many USDS recruits are on contracts extending into this year and even beyond. The USDS budget, part of the continuing resolution that keeps the government functioning, will continue. And as the efforts of the tech teams inside various agencies are increasingly appreciated, the career administrators will undoubtedly tell the incoming political appointees that the continuation of these programs will be to their benefit. In other words, quite intentionally, the USDS and its cousins have dug themselves into the federal government.

Still, these programs depend on a continuing pipeline. Todd Park concedes that there has been a pause in signups since the election, as people determine whether the new administration is committed to the programs. (He does say that the people he has targeted as potential Presidential Innovation Fellows for 2017 have told him they still intend to apply.) [Update: USDS clarifies that though there has been a dropoff, applications are still coming in. So maybe not a pause.] Even if the new administration continues the programs, would idealistic coders and designers come to Washington to work for Donald Trump? So far, those recruiting for the next wave haven’t found a definitive answer. “I always give them the spiel that most of us didn’t come here to serve Obama, but to serve the American people,” says Jeff Maher, who works on the USDS team inside the VA. “There’s still a lot of work to do and the American people want that to happen.” Jen Pahlka says that although it’s complicated to work under a president whose values you don’t endorse, it’s important that individuals with values you do endorse are working for the people. “He doesn’t own the government,” she says. “We own the government.”

Rob Cook, who took his post heading TTS a week before the election, says he has no buyer’s remorse. “I didn’t come here for a partisan reason,” he says. “It’s really important that the government gets into the 21st century. This is a long-term initiative, because technology does not stop changing. It ought to be here through many, many administrations.”

Still, many idealistic coders will simply not have anything to do with a Trump White House. In fact, some current tech surge people who would otherwise be recruiting newcomers have refused. “I wouldn’t recommend my friends come here,” says one. “I knew what a crazy three-ring circus it was when we were working for the good guys.”

The biggest fear is that the nature of the work will change. The tech surge took satisfaction in creating systems that simplified access to medical care, produced easier ways to pay taxes, and created less confusing ways to immigrate to the United States. Its members now fear that tasks in the Trump era might involve projects anathema to their morals. Would USDS and 18F be asked to improve software to deny health care to people, deport children, or even create a Muslim registry? Though it seems like an unlikely job to assign to short-term Silicon Valley stars who want to make a positive difference, the latter is a real fear, cited by multiple people inside the Obama team whom I spoke to as a scenario that would kill the USDS. “It would be an honorable way to go out,” says one insider.

As the inauguration approaches, the mood swings at the USDS are Calder-esque. Dickerson describes it as “a high school graduation and a massive layoff mixed with a funeral that’s gone on for two months.” On the Facebook feeds of politically appointed tech surgers you see photos of final handshakes with the president; they’re wearing uncharacteristically formal garb and are often with their families; they have been ushered into the Oval Office for mutual thanks. Obama himself bid farewell to the team at a ceremony on the steps of the Executive Office Building last Thursday. He spent the better part of an hour thanking the team and telling them what a difference they made.

But they know it already, and the experience has made many of them reluctant to return to their previous lives inside profit-making corporations. Those jobs don’t seem so meaningful anymore. Some are sticking around the DC area, even though they hate it as a place to live. There’s talk about a loose network of tech surge alumni engaging in a new kind of insurgency — outside the government but with the same end of serving the people.

“Every hint I ever had was that the infrastructure of civilization was someone else’s problem,” says Matthew Weaver. “What a lie that was. It was my problem. I’m lucky to have the skills to address this. Now I want everyone who has an inkling of this to understand…to say, this is my problem.”